FI86723C - Förfarande för framställning av terapeutiskt användbara 2,3-dihydro-2- oxo-1H-imidazo/4,5-b/kinolinyleterderivat - Google Patents
Förfarande för framställning av terapeutiskt användbara 2,3-dihydro-2- oxo-1H-imidazo/4,5-b/kinolinyleterderivat Download PDFInfo
- Publication number
- FI86723C FI86723C FI872220A FI872220A FI86723C FI 86723 C FI86723 C FI 86723C FI 872220 A FI872220 A FI 872220A FI 872220 A FI872220 A FI 872220A FI 86723 C FI86723 C FI 86723C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- aromatic
- imidazo
- dihydro
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (6)
1. Förfarande för framställning av terapeutiskt användbara 2,3-dihydro-2-oxo-lH-imidazo[4,5-b]kinolinyl-5 eterderivat med formeln R2-F I VN\ I II \ }=o (i) 10 \ Alk-Y 1 i vilken I*! är väte eller nedre alkyl;
15 R2 är väte eller halogen; Alk är en alkylenkedja som innehäller 1-5 kolato- mer; Y är hydroxyl, hydroxyl, som har förestrats med en alkansyra, som innehäller 1-6 kolatomer, en alkoxi, var-20 vid antalet kolatomer av gruppen Alk-Y är 2 - 10, acetyl, di(nedre alkyl)amino, -C02H, -C02R3, i vilken R3 är nedre alkyl, gruppen 1 2 3 4 5 6 7 8 9 10 2 i vilken R4 är väte, nedre alkyl eller gruppen -(CH2)nC02R6, 3 i vilken n är heltalet 1-8 och R6 är nedre alkyl, och R5 4 är väte, nedre alkyl, adamantanamyl eller en cykloalkyl, 5 som innehäller 3-7 kolatomer, eller R4 och R5 tillsam- 6 mans bildar morfolinyl, piperidinyl, som eventuellt är 7 substituerad med gruppen -C02R7, i vilken R7 är nedre al 8 kyl, 4-fenylpiperazinylin, gruppen 9 /-N_R8 10
35 Yj___0 , i vilken R8 är nedre alkyl, 94 86723 gruppen OH -CHCH2NH-R8, i vilken R8 är nedre alkyl eller gruppen N — N -H
5 -N R9 i vilken R9 är nedre alkyl, eller en cyk-loalkyl, son* inneh&ller 5-7 kolatomer, eller -S02-fenyl, eller för framställning av deras farmaceutiskt godtagbara salter, kännetecknat därav, att 10 a) en substltuerad hydantoin med formeln NO, " r jTY 2 N\ -ic (II) 15 0 — , \ N Alk-Y 1 i vilken Aik, R2/ R2 och Y är ovan definierade, reduceras, varvid den önskade föreningen med formeln I och/eller en 20 förening med formeln H R2-r T T Vo (ιιβ) 25 \ \ Alk-Y i vilken Aik, R2, R2 och Y är ovan definierade, och/eller en förening med formeln
30 N « 'i—tJ Y'\ di-) \ " \ Alk-Y 1 i vilken Aik, Rt, R2 och Y är ovan definierade, erhälls,
95 B6723 varefter vid behov b) föreningen enligt formeln IIa, som erhällits i steget a), behandlas med oxidationmedel, varvid den önska-de föreningen med formeln X och/eller den ovan erhällna 5 föreningen enligt formeln IIb erhälls; och vid behov (c) föreningen enligt formeln IIb, som erhällits i steget a) eller b), dehydras; och om sä önskas (i) föreningen med formeln I, i vilken Y är -C02H, förvandlas till en motsvarande amid eller ester; eller 10 (ii) föreningen enligt formeln I, i vilken Y är -C02R3, hydrolyseras till en motsvarande karboxylsyra; eller (iii) en förening med formeln I, i vilken Y är OH, bringas att reagera med en alkansyra, som innehäller 1-6 15 kolatomer, varvid en motsvarande ester erhälls; eller (iv) en förening med formeln I, i vilken Y är oxo, som bildar keton, reduceras till en motsvarande alkohol; eller (v) en förening med formeln I, i vilken Y är grup- 20 pen -CH- förvandlas till en motsvarande aminoalkohol, i vilken Y är 25 OH -CHCH2NH-R8 genom katalytisk hydrolysering av en motsvarande cyklicerad karbamat; och om sä önskas (d) föreningen med formeln I, som erhällits som fri bas, förvandlas till sitt farmaceutiskt godtagbara salt. 30 2. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att föreningen N-cyklohexyl-N-(4-[ ( 2,3-dihydro-2-oxo-lH-imidazo- [4,5-b] kinolin-7-yl )oxi] -1-oxobutyl)glysinmetylester eller dess farmaceutiskt godtagbara salt framställs. 35 3. Förfarande enligt patentkravet 1, känne- 96 86 723 t e c k n a t därav, att föreningen N-cyklohexyl-N-metyl- 4- [(2,3-dihydro-2-oxo-lH-imidazo[4,5-b]kinolin-7-yl)oxi]-butanamid eller dess farmaceutiskt godtagbara salt frams-tälls. 5 4. Förfarande enligt patentkravet 1, k ä n n e - t e c k n a t därav, att föreningen N-cyklohexyl-N-metyl- 5- [(2,3-dihydro-2-oxo-lH-imidazo[4,5-b]kinolin-7-yl)oxi]-pentanamid eller dess farmaceutiskt godtagbara salt frams-tälls. 10 5. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att föreningen N-cykloheptyl-N-me-tyl-5-[(2,3-dihydro-2-oxo-lH-imidazo[4,5-b]kinolin-7-yl)-oxi]pentanamid eller dess farmaceutiskt godtagbara salt framställs.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/866,813 US4775674A (en) | 1986-05-23 | 1986-05-23 | Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors |
| US86681386 | 1986-05-23 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI872220A0 FI872220A0 (fi) | 1987-05-20 |
| FI872220A FI872220A (fi) | 1987-11-24 |
| FI86723B FI86723B (fi) | 1992-06-30 |
| FI86723C true FI86723C (sv) | 1992-10-12 |
Family
ID=25348473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI872220A FI86723C (sv) | 1986-05-23 | 1987-05-20 | Förfarande för framställning av terapeutiskt användbara 2,3-dihydro-2- oxo-1H-imidazo/4,5-b/kinolinyleterderivat |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4775674A (sv) |
| JP (1) | JPS62283972A (sv) |
| KR (1) | KR900008567B1 (sv) |
| AT (1) | AT392790B (sv) |
| AU (1) | AU603577B2 (sv) |
| BE (1) | BE1002033A4 (sv) |
| CA (1) | CA1289137C (sv) |
| CH (1) | CH675246A5 (sv) |
| DE (1) | DE3717291A1 (sv) |
| DK (1) | DK166084C (sv) |
| ES (1) | ES2005588A6 (sv) |
| FI (1) | FI86723C (sv) |
| FR (1) | FR2603586B1 (sv) |
| GB (1) | GB2190676B (sv) |
| GR (1) | GR870803B (sv) |
| HU (1) | HU197570B (sv) |
| IL (1) | IL82612A0 (sv) |
| IT (1) | IT1205031B (sv) |
| LU (1) | LU86896A1 (sv) |
| NL (1) | NL8701226A (sv) |
| NZ (1) | NZ220345A (sv) |
| PT (1) | PT84938B (sv) |
| SE (1) | SE465163B (sv) |
| ZA (1) | ZA873583B (sv) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1306260C (en) * | 1985-10-18 | 1992-08-11 | Shionogi & Co., Ltd. | Condensed imidazopyridine derivatives |
| JPH01189791A (ja) * | 1988-01-26 | 1989-07-28 | New Japan Radio Co Ltd | 非接触ｉｄカード |
| US4943573A (en) * | 1989-11-01 | 1990-07-24 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyloxyalkanoic acid amides with enhanced water solubility |
| US5262540A (en) * | 1989-12-20 | 1993-11-16 | Bristol-Myers Squibb Company | [2(4,5-diaryl-2 oxazoyl substituted phenoxy alkanoic acid and esters |
| PH31245A (en) * | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US5552267A (en) * | 1992-04-03 | 1996-09-03 | The Trustees Of Columbia University In The City Of New York | Solution for prolonged organ preservation |
| US5196428A (en) * | 1992-04-03 | 1993-03-23 | Bristol-Myers Squibb Company | Imidazo[4,5-b]qinolinyl oxy alkyl ureas |
| US5187188A (en) * | 1992-04-03 | 1993-02-16 | Bristol-Myers Squibb Company | Oxazole carboxylic acid derivatives |
| US5348960A (en) * | 1992-04-03 | 1994-09-20 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyl oxy alkyl tetrazolyl piperidine derivatives |
| US5158958A (en) * | 1992-04-03 | 1992-10-27 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyl oxy alkyl sulfonyl piperidine derivatives |
| US5208237A (en) * | 1992-04-03 | 1993-05-04 | Bristol-Meyers Squibb Company | 7-oxypropylsulfonamido-imidazo[4,5-b]quinolin-2-ones |
| TW593317B (en) | 1993-06-21 | 2004-06-21 | Janssen Pharmaceutica Nv | Positive cardiac inotropic and lusitropic pyrroloquinolinone derivatives |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| JP4767429B2 (ja) * | 2001-03-02 | 2011-09-07 | 株式会社クラレ | 架橋剤および架橋性重合体 |
| JP2006509790A (ja) * | 2002-11-27 | 2006-03-23 | アルテシアン セラピューティック，インコーポレイティド | 心不全の治療のための混合されたＰＤＥ阻害およびβアドレナリン拮抗薬活性または部分的作用薬活性を有する化合物 |
| MXPA06001669A (es) | 2003-08-12 | 2006-04-28 | 3M Innovative Properties Co | Compuestos que contienen imidazo-oxima sustituidos. |
| US7897597B2 (en) | 2003-08-27 | 2011-03-01 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| WO2005023190A2 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| CA2545774A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
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| JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| AU2006210392A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune response modifiers |
| JP2008530113A (ja) | 2005-02-11 | 2008-08-07 | コーリー ファーマシューティカル グループ，インコーポレイテッド | オキシムおよびヒドロキシラミン置換イミダゾ［４，５−ｃ］環化合物および方法 |
| AU2006232377A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| WO2006107851A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7906506B2 (en) | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
| US8227603B2 (en) | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
| US8299248B2 (en) | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| EP2995619B1 (en) | 2006-08-02 | 2019-09-25 | Cytokinetics, Inc. | Certain chemical entities comprising imidazopyrimidines, compositions and methods |
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| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US7851484B2 (en) | 2007-03-30 | 2010-12-14 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| KR101951220B1 (ko) | 2011-07-13 | 2019-02-22 | 싸이토키네틱스, 인코포레이티드 | 조합 als 치료법 |
| US20150119399A1 (en) | 2012-01-10 | 2015-04-30 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| WO2024149378A1 (zh) * | 2023-01-13 | 2024-07-18 | 上海超阳药业有限公司 | 喹啉酮化合物和萘啶酮化合物及其用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932407A (en) * | 1973-11-19 | 1976-01-13 | Bristol-Myers Company | Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones |
| NL7807507A (nl) * | 1977-07-25 | 1979-01-29 | Hoffmann La Roche | Tricyclische verbindingen. |
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| US4668686A (en) * | 1985-04-25 | 1987-05-26 | Bristol-Myers Company | Imidazoquinoline antithrombrogenic cardiotonic agents |
-
1986
- 1986-05-23 US US06/866,813 patent/US4775674A/en not_active Expired - Fee Related
-
1987
- 1987-05-15 AU AU72993/87A patent/AU603577B2/en not_active Ceased
- 1987-05-18 NZ NZ220345A patent/NZ220345A/xx unknown
- 1987-05-19 GB GB8711839A patent/GB2190676B/en not_active Expired - Fee Related
- 1987-05-19 ZA ZA873583A patent/ZA873583B/xx unknown
- 1987-05-20 FI FI872220A patent/FI86723C/sv not_active IP Right Cessation
- 1987-05-21 GR GR870803A patent/GR870803B/el unknown
- 1987-05-21 IL IL82612A patent/IL82612A0/xx not_active IP Right Cessation
- 1987-05-22 DE DE19873717291 patent/DE3717291A1/de not_active Withdrawn
- 1987-05-22 NL NL8701226A patent/NL8701226A/nl not_active Application Discontinuation
- 1987-05-22 PT PT84938A patent/PT84938B/pt unknown
- 1987-05-22 CA CA000537720A patent/CA1289137C/en not_active Expired - Fee Related
- 1987-05-22 BE BE8700581A patent/BE1002033A4/fr not_active IP Right Cessation
- 1987-05-22 IT IT20650/87A patent/IT1205031B/it active
- 1987-05-22 DK DK263587A patent/DK166084C/da active
- 1987-05-22 JP JP62125642A patent/JPS62283972A/ja active Pending
- 1987-05-22 AT AT1320/87A patent/AT392790B/de not_active IP Right Cessation
- 1987-05-22 ES ES8701506A patent/ES2005588A6/es not_active Expired
- 1987-05-22 FR FR878707252A patent/FR2603586B1/fr not_active Expired - Fee Related
- 1987-05-22 KR KR1019870005066A patent/KR900008567B1/ko not_active IP Right Cessation
- 1987-05-22 SE SE8702158A patent/SE465163B/sv not_active IP Right Cessation
- 1987-05-22 HU HU872295A patent/HU197570B/hu not_active IP Right Cessation
- 1987-05-22 LU LU86896A patent/LU86896A1/fr unknown
- 1987-05-25 CH CH2018/87A patent/CH675246A5/de not_active IP Right Cessation
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